Ozonolysis of the double bond of the unsaturated uronate residue in low molecular weight heparin and K5 heparosan

Masuko, Sayaka
Higashi, Kyohei
Wang, Zhenyu
Bhaskar, Ujjwal
Hickey, Anne Marie
Zhang, Fuming
Toida, Toshihiko
Dordick, Jonathan S.
Linhardt, Robert J.
Thumbnail Image
Other Contributors
Issue Date
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Terms of Use
In Copyright : this Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). https://rightsstatements.org/page/InC/1.0/
Full Citation
Ozonolysis of the double bond of the unsaturated uronate residue in low molecular weight heparin and K5 heparosan, S. Masuko, K. Higashi, Z. Wang, U. Bhaskar, A. M. Hickey, F. Zhang, T. Toida, J. S. Dordick, R. J. Linhardt, Carbohydrate Research, 346, 1962–1966, 2011.
Ozone is known to add across and cleave carbon-carbon double bonds. Ozonolysis is widely used for the preparation of pharmaceuticals, for bleaching substances and for killing microorganisms in air and water sources. Some polysaccharides and oligosaccharides, such as those prepared using chemical or enzymatic β-elimination, contain a site of unsaturation. We examined ozonolysis of low-molecular-weight heparins (LMWHs), enoxaparin and logiparin, and heparosan oligo- and polysaccharides for the removal of the nonreducing terminal unsaturated uronate residue. 1D (1)H NMR showed that these ozone-treated polysaccharides retained the same structure as the starting polysaccharide, except that the C4-C5 double bond in the nonreducing end unsaturated uronate had been removed. The anticoagulant activity of the resulting product from enoxaparin and logiparin was comparable to that of the starting material. These results demonstrate that ozonolysis is an important tool for the removal of unsaturated uronate residues from LMWHs and heparosan without modification of the core polysaccharide structure or diminution of anticoagulant activity. This reaction also has potential applications in the chemoenzymatic synthesis of bioengineered heparin from Escherichia coli-derived K5 heparosan.
Carbohydrate Research, 346, 1962–1966
Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
Carbohydrate Research
A full text version is available in DSpace@RPI